Hydrochloric Acid → HCID 69084168, compound

HRID 1468634Notes

Reaction equation

HRID 1468634 reaction equation
Cl.[CH2:2]([C@@:5]1([OH:29])[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@@H:6]1[O:27][CH3:28])[CH:3]=[CH2:4]>>[C:11]([O:29][C@:5]1([CH2:2][CH:3]=[CH2:4])[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@@H:6]1[O:27][CH3:28])(=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66688035HCID 66688035, compound

Product 1

HCID 69084168HCID 69084168, compound

Procedure

The reaction mixture was then stirred with 1 N HCl and extracted with dichloro-methane. The organic layers were combined and washed with saturated aqueous NaHCO3 followed by brine. After drying with MgSO4, filtration and evaporation of the volatiles, the residue was purified by column chromatography (400 g silica) eluting with heptane to 15% ethyl acetate in heptane to give reaction product as an oil (as a mixture with compound 5). The mixture was purified again with CH2Cl2 as eluent (400 g silica). The pure fractions were collected and intermediate 6 was obtained as a colorless oil (13.05 g, 39%). HPLC Condition A, Rt: 3.41 min, m/z=457 (M-OMe)+. 1H NMR (400 MHz, CDCl3) δ ppm 8.1 (d, 2H, J=7.9 Hz), 7.68-7.28 (m, 13H), 5.84-5.77 (m, 1H), 5.12 (d, 1H, J=16 Hz), 4.95 (d, 1H, J=16 Hz), 4.92 (d, 1H, J=12.3 Hz), 4.56 (d, 1H, J=12.3 Hz), 4.48 (d, 1H, J=11.6 Hz), 4.40 (d, 1H, J=11.6 Hz), 4.2 (m, 1H), 3.85 (d, 1H, J=6.2 Hz), 3.53 (d, 1H, J=10.8 Hz), 3.7 (s, 3H), 3.45 (dd, 1H, J=10.8, 6.2 Hz), 3.25 (dd, 1H, J=15.5, 7.3 Hz), 2.45 (dd, 1H, J=15.5, 7.3 Hz).

Workup

  1. extractionextracted with dichloro-methane
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialAfter drying with MgSO4, filtration and evaporation of the volatiles
  4. customthe residue was purified by column chromatography (400 g silica)
  5. washeluting with heptane to 15% ethyl acetate in heptane
  6. customto give
  7. customThe mixture was purified again with CH2Cl2 as eluent (400 g silica)
  8. customThe pure fractions were collected

Sources & evidence

ORD record
ord-8cf711247b7741afaf39974b7c3ed4b7
Source dataset
uspto-grants-2015_04
Patent number
US09006209B2

Reaction notes

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